Nature crafts many molecules from common precursors, but this approach isn't always possible in chemical synthesis. A strategy for synthesizing a family of natural products succeeds by ignoring nature's blueprint. See Article p.461
Polyphenols are a group of structurally diverse compounds found in fruits, vegetables and plant-based food products such as tea, wine and chocolate. Because many polyphenols are antioxidants, they have been acclaimed as natural health-protecting agents, although the benefits to humans have yet to be proven. Nevertheless, some polyphenols have biological activities that make them potentially useful leads in the search for drugs against illnesses such as heart disease, cancer and Alzheimer's disease. Pharmaceutical research has been thwarted, however, by the fact that the most complex polyphenols are available from their natural sources in only limited quantities.
An obvious solution would be to prepare large quantities of polyphenols using chemical synthesis. This might seem a trivial task, given that many polyphenols are oligomers derived from just one or two precursor molecules, of which resveratrol (Fig. 1) is perhaps the best-known example. In fact, the structural complexity of resveratrol oligomers makes their chemical synthesis a daunting challenge. But on page 461 of this issue, Snyder et al.1 describe a major advance in polyphenol research: a daring but clever synthetic strategy that has enabled them to prepare a series of resveratrol trimers and tetramers — the highest-order resveratrol oligomers prepared to date.